3-(2-benzo[b]furan-2-yl-2-oxoethyl)-2H-[1,2,4]triazino-[2,3-c]quinazolin-2-one | 940238-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(2-benzo[b]furan-2-yl-2-oxoethyl)-2H-[1,2,4]triazino-[2,3-c]quinazolin-2-one
• 英文别名: 3-[2-(1-Benzofuran-2-yl)-2-oxoethyl]-[1,2,4]triazino[2,3-c]quinazolin-2-one
• CAS: 940238-49-3
• 化学式: C₂₀H₁₂N₄O₃
• 分子量: 356.34
• InChiKey: ULQLGLHZDOEKRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  87.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-benzo[b]furan-2-yl-2-oxoethyl)-2H-[1,2,4]triazino-[2,3-c]quinazolin-2-one 在 hydrazine hydrate 作用下， 以 异丙醇 为溶剂， 以86%的产率得到3'-(2-aminophenyl)-3-(benzo[b]furan-2-yl)-spiro-[pyrazoline-5,6'(1'H)-1,2,4-triazin]-5'(4'H)-one
  参考文献：
  名称：

  Synthesis of spiro-fused (C5)-pyrazolino-(C6)-triazinones, a new heterocyclic system

  摘要：

  Reaction of 4-hydrazinoquinazoline with 2,4-diketoesters gives the corresponding 3-acylmethyl-2H[1,2,4]triazino[2,3-c]quinazolin-2-ones in a one-step procedure via cyclocondensation-Dimroth-like rearrangement. Spectroscopic studies as well as X-ray analysis reveal that the obtained triazinoquinazolines exist in their ketoimine tautomeric form. Treatment of these compounds with hydrazine hydrate affords 3'-(2-aminophenyl)-3-(het)aryl-spiro[pyrazoline-5,6'(1'H)-1,2,4-triazin]-5'(4'H)-ones or 5-(het)arylpyrazole-3-carboxylic acid hydrazides depending on the reaction conditions. The structure of the spiro-heterocycles was elucidated by means of single-crystal X-ray analysis and confirmed by spectroscopic investigations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.091
• 作为产物：
  描述：

  4-肼基喹唑啉 、 methyl 4-(benzofuran-2-yl)-2,4-dioxobutanoate 以 溶剂黄146 为溶剂， 以49%的产率得到3-(2-benzo[b]furan-2-yl-2-oxoethyl)-2H-[1,2,4]triazino-[2,3-c]quinazolin-2-one
  参考文献：
  名称：

  Synthesis of spiro-fused (C5)-pyrazolino-(C6)-triazinones, a new heterocyclic system

  摘要：

  Reaction of 4-hydrazinoquinazoline with 2,4-diketoesters gives the corresponding 3-acylmethyl-2H[1,2,4]triazino[2,3-c]quinazolin-2-ones in a one-step procedure via cyclocondensation-Dimroth-like rearrangement. Spectroscopic studies as well as X-ray analysis reveal that the obtained triazinoquinazolines exist in their ketoimine tautomeric form. Treatment of these compounds with hydrazine hydrate affords 3'-(2-aminophenyl)-3-(het)aryl-spiro[pyrazoline-5,6'(1'H)-1,2,4-triazin]-5'(4'H)-ones or 5-(het)arylpyrazole-3-carboxylic acid hydrazides depending on the reaction conditions. The structure of the spiro-heterocycles was elucidated by means of single-crystal X-ray analysis and confirmed by spectroscopic investigations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.091

文献信息

• Synthesis of spiro-fused (C5)-pyrazolino-(C6)-triazinones, a new heterocyclic system
  作者：Alexander V. Karpenko、Sergey I. Kovalenko、Oleg V. Shishkin

  DOI：10.1016/j.tet.2009.05.091

  日期：2009.8

  Reaction of 4-hydrazinoquinazoline with 2,4-diketoesters gives the corresponding 3-acylmethyl-2H[1,2,4]triazino[2,3-c]quinazolin-2-ones in a one-step procedure via cyclocondensation-Dimroth-like rearrangement. Spectroscopic studies as well as X-ray analysis reveal that the obtained triazinoquinazolines exist in their ketoimine tautomeric form. Treatment of these compounds with hydrazine hydrate affords 3'-(2-aminophenyl)-3-(het)aryl-spiro[pyrazoline-5,6'(1'H)-1,2,4-triazin]-5'(4'H)-ones or 5-(het)arylpyrazole-3-carboxylic acid hydrazides depending on the reaction conditions. The structure of the spiro-heterocycles was elucidated by means of single-crystal X-ray analysis and confirmed by spectroscopic investigations. (C) 2009 Elsevier Ltd. All rights reserved.